Sodium Hydroxide → HCID 19966124, compound

HRID 977875Notes

Reaction equation

HRID 977875 reaction equation
[OH-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13]C(=O)C)[C:7]=1[NH:17][C:18](=[O:34])[CH2:19][CH:20]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:27][C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH3:5])[CH3:4]>O.CO>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[C:7]=1[NH:17][C:18](=[O:34])[CH2:19][CH:20]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[O:27][C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19966041HCID 19966041, compound

Product 1

HCID 19966124HCID 19966124, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 79 mg (1.98 mmol) of sodium hydroxide in 1 ml of water was added to a solution of 567 mg (1.32 mmol) of N-(2-isopropyl-6-acetoxymethylphenyl)-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (v) above] in 15 ml of methanol, and the resulting mixture was stirred for 1 hour at room temperature. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the concentrate was partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous solution of sodium chloride, and the solvent was removed by distillation under reduced pressure, to give 511 mg (a quantitative yield) of the title compound, melting at 155°-156° C. (after recrystallization from a mixture of ethyl acetate and hexane).

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe concentrate was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with a saturated aqueous solution of sodium chloride
  4. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-acc2bda64e124d76bc184daa773e7d0d
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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